Tetrahydrofuran → HCID 21474801, compound

HRID 2294359Notes

Reaction equation

HRID 2294359 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH:18]([CH3:20])[CH3:19])[C:14](OC)=[O:15])[CH2:8]1.[BH4-].[Li+].O1CCCC1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH:18]([CH3:19])[CH3:20])[CH2:14][OH:15])[CH2:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 21474780HCID 21474780, compound

Product 1

HCID 21474801HCID 21474801, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Preparation 5 was repeated, except that 0.93 g of methyl 2-[5-(3-chlorophenoxymethyl)-2-oxooxazolidin-3-yl]-3-methylbutanoate (polar isomer), obtained as described in Preparation 99, 118 mg of lithium borohydride, 10 ml of anhydrous tetrahydrofuran and 87 mg of anhydrous methanol were used, to give 0.47 g of the title compound having an Rf value of 0.48 (on silica gel thin layer chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as the developing solvent) from the polar diastereomer.

Workup

  1. customA procedure similar to that described in Preparation 5
  2. customobtained

Sources & evidence

ORD record
ord-cede7529453d450a8d8ac515b4c14d74
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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